Catalytic Asymmetric Intermolecular [3 + 2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins

An enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis is reported. A dual catalyst system involving DPZ and a chiral phosphoric acid is effective for the transfo...

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Bibliographic Details
Published in:Organic letters 2023-06, Vol.25 (24), p.4551-4555
Main Authors: Dai, Yating, Huang, Hongchun, Liang, Shuangshuang, Yin, Yanli, Ban, Xu, Zhao, Xiaowei, Jiang, Zhiyong
Format: Article
Language:English
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Summary:An enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis is reported. A dual catalyst system involving DPZ and a chiral phosphoric acid is effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee’s, and drs. Among them, elaborate modulation of the ester group of 2-aryl acrylates was shown to be effective in improving reactivity, thereby enabling the success of the transformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01585